CS199508B2 - Process for preparing copolymers of ethylene with one or more polyene hydrocarbons - Google Patents
Process for preparing copolymers of ethylene with one or more polyene hydrocarbons Download PDFInfo
- Publication number
- CS199508B2 CS199508B2 CS774674A CS467477A CS199508B2 CS 199508 B2 CS199508 B2 CS 199508B2 CS 774674 A CS774674 A CS 774674A CS 467477 A CS467477 A CS 467477A CS 199508 B2 CS199508 B2 CS 199508B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- vanadium
- compounds
- reaction
- ethylene
- group
- Prior art date
Links
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000005977 Ethylene Substances 0.000 title claims abstract description 24
- 229920001577 copolymer Polymers 0.000 title claims abstract description 15
- -1 polyene hydrocarbons Chemical class 0.000 title claims abstract description 12
- 229930195733 hydrocarbon Natural products 0.000 title claims abstract description 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 229910052720 vanadium Inorganic materials 0.000 claims abstract description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims abstract description 12
- 150000003682 vanadium compounds Chemical class 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 10
- 230000003197 catalytic effect Effects 0.000 claims abstract description 7
- 150000002894 organic compounds Chemical class 0.000 claims abstract description 6
- 125000003367 polycyclic group Chemical group 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002877 alkyl aryl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 150000005840 aryl radicals Chemical group 0.000 claims abstract description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052794 bromium Chemical group 0.000 claims abstract description 4
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 4
- 239000000460 chlorine Substances 0.000 claims abstract description 4
- VUNCWTMEJYMOOR-UHFFFAOYSA-N hexachlorocyclopentadiene Chemical compound ClC1=C(Cl)C(Cl)(Cl)C(Cl)=C1Cl VUNCWTMEJYMOOR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000012429 reaction media Substances 0.000 claims abstract description 3
- 239000012066 reaction slurry Substances 0.000 claims abstract 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 32
- 239000000047 product Substances 0.000 claims description 19
- 239000003054 catalyst Substances 0.000 claims description 15
- 238000006116 polymerization reaction Methods 0.000 claims description 13
- 239000002904 solvent Substances 0.000 claims description 9
- 229910052782 aluminium Inorganic materials 0.000 claims description 5
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical class [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 238000005119 centrifugation Methods 0.000 claims 1
- 238000001704 evaporation Methods 0.000 claims 1
- 230000008020 evaporation Effects 0.000 claims 1
- 238000002844 melting Methods 0.000 abstract description 10
- 230000008018 melting Effects 0.000 abstract description 10
- 239000000178 monomer Substances 0.000 abstract description 7
- 239000004698 Polyethylene Substances 0.000 abstract description 2
- 229920000573 polyethylene Polymers 0.000 abstract description 2
- 238000005406 washing Methods 0.000 abstract description 2
- 150000001399 aluminium compounds Chemical class 0.000 abstract 1
- 229940077746 antacid containing aluminium compound Drugs 0.000 abstract 1
- XTKDAFGWCDAMPY-UHFFFAOYSA-N azaperone Chemical compound C1=CC(F)=CC=C1C(=O)CCCN1CCN(C=2N=CC=CC=2)CC1 XTKDAFGWCDAMPY-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 54
- 229920000642 polymer Polymers 0.000 description 24
- 239000000203 mixture Substances 0.000 description 21
- 239000000243 solution Substances 0.000 description 16
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 14
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 12
- OJOWICOBYCXEKR-UHFFFAOYSA-N 5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=CC)CC1C=C2 OJOWICOBYCXEKR-UHFFFAOYSA-N 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 8
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 7
- NSWUXAUIAZVROT-UHFFFAOYSA-N 1-(2-cyclopenta-1,3-dien-1-ylpropan-2-yl)cyclopenta-1,3-diene Chemical compound C=1C=CCC=1C(C)(C)C1=CC=CC1 NSWUXAUIAZVROT-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
- 229910052717 sulfur Inorganic materials 0.000 description 6
- 239000011593 sulfur Substances 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- YNLAOSYQHBDIKW-UHFFFAOYSA-M diethylaluminium chloride Chemical compound CC[Al](Cl)CC YNLAOSYQHBDIKW-UHFFFAOYSA-M 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 150000004291 polyenes Chemical class 0.000 description 3
- 239000002002 slurry Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- OJOWICOBYCXEKR-KRXBUXKQSA-N (5e)-5-ethylidenebicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(=C/C)/CC1C=C2 OJOWICOBYCXEKR-KRXBUXKQSA-N 0.000 description 2
- JESYUGLAAYESAZ-UHFFFAOYSA-N 2,3-dimethyl-1-penta-1,3-dienylbicyclo[2.2.1]hept-2-ene Chemical compound CC1=C(C2(CCC1C2)C=CC=CC)C JESYUGLAAYESAZ-UHFFFAOYSA-N 0.000 description 2
- IKEHOXWJQXIQAG-UHFFFAOYSA-N 2-tert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1 IKEHOXWJQXIQAG-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 229920001903 high density polyethylene Polymers 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 229910001220 stainless steel Inorganic materials 0.000 description 2
- 239000010935 stainless steel Substances 0.000 description 2
- 125000005287 vanadyl group Chemical group 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- UDWASUCJIKKBLS-NSCUHMNNSA-N (3e)-1,1,2,3,4,5-hexachloropenta-1,3-diene Chemical compound ClC\C(Cl)=C(/Cl)C(Cl)=C(Cl)Cl UDWASUCJIKKBLS-NSCUHMNNSA-N 0.000 description 1
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 1
- GWHRPSOIZQENQQ-UHFFFAOYSA-N 5-chlorocyclopenta-1,3-diene Chemical compound ClC1C=CC=C1 GWHRPSOIZQENQQ-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910021550 Vanadium Chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- HQMRIBYCTLBDAK-UHFFFAOYSA-M bis(2-methylpropyl)alumanylium;chloride Chemical compound CC(C)C[Al](Cl)CC(C)C HQMRIBYCTLBDAK-UHFFFAOYSA-M 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- JJSGABFIILQOEY-UHFFFAOYSA-M diethylalumanylium;bromide Chemical compound CC[Al](Br)CC JJSGABFIILQOEY-UHFFFAOYSA-M 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 230000005484 gravity Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- VVYHREKHNQJVTG-UHFFFAOYSA-N hexane vanadium Chemical compound CCCCCC.[V] VVYHREKHNQJVTG-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000003562 lightweight material Substances 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- JFNLZVQOOSMTJK-KNVOCYPGSA-N norbornene Chemical compound C1[C@@H]2CC[C@H]1C=C2 JFNLZVQOOSMTJK-KNVOCYPGSA-N 0.000 description 1
- RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- WJMCBYIVZMZKLP-UHFFFAOYSA-N toluene vanadium Chemical compound [V].C1(=CC=CC=C1)C WJMCBYIVZMZKLP-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 238000004073 vulcanization Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/12—Polymerisation in non-solvents
- C08F2/14—Organic medium
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
- C08F210/02—Ethene
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT25379/76A IT1064663B (it) | 1976-07-16 | 1976-07-16 | Procedimento per la preparazione in alta resa di copolimeri dell etilene con polieni |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS199508B2 true CS199508B2 (en) | 1980-07-31 |
Family
ID=11216523
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS774674A CS199508B2 (en) | 1976-07-16 | 1977-07-13 | Process for preparing copolymers of ethylene with one or more polyene hydrocarbons |
Country Status (20)
-
1976
- 1976-07-16 IT IT25379/76A patent/IT1064663B/it active
-
1977
- 1977-07-06 IL IL52475A patent/IL52475A/xx unknown
- 1977-07-07 GB GB35803/79A patent/GB1589097A/en not_active Expired
- 1977-07-07 GB GB28622/77A patent/GB1589095A/en not_active Expired
- 1977-07-07 GB GB35802/79A patent/GB1589096A/en not_active Expired
- 1977-07-07 AU AU26852/77A patent/AU512515B2/en not_active Expired
- 1977-07-07 CA CA282,224A patent/CA1112799A/en not_active Expired
- 1977-07-13 DD DD7700200041A patent/DD130483A5/xx unknown
- 1977-07-13 NL NL7707832A patent/NL7707832A/xx not_active Application Discontinuation
- 1977-07-13 CS CS774674A patent/CS199508B2/cs unknown
- 1977-07-13 FR FR7721715A patent/FR2358429A1/fr active Granted
- 1977-07-14 YU YU01749/77A patent/YU174977A/xx unknown
- 1977-07-14 CH CH873977A patent/CH628909A5/it not_active IP Right Cessation
- 1977-07-14 JP JP8363777A patent/JPS5311983A/ja active Pending
- 1977-07-14 NO NO772510A patent/NO147214C/no unknown
- 1977-07-14 LU LU77761A patent/LU77761A1/xx unknown
- 1977-07-15 SE SE7708247A patent/SE7708247L/xx not_active Application Discontinuation
- 1977-07-15 ZA ZA00774264A patent/ZA774264B/xx unknown
- 1977-07-15 DK DK323377A patent/DK323377A/da not_active Application Discontinuation
- 1977-07-15 DE DE19772732110 patent/DE2732110A1/de not_active Withdrawn
- 1977-07-15 HU HU77SA3047A patent/HU178728B/hu unknown
- 1977-07-15 BE BE179391A patent/BE856867A/xx not_active IP Right Cessation
-
1982
- 1982-07-05 YU YU01458/82A patent/YU145882A/xx unknown
- 1982-07-05 YU YU01457/82A patent/YU145782A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LU77761A1 (enrdf_load_stackoverflow) | 1977-10-17 |
| FR2358429A1 (fr) | 1978-02-10 |
| AU2685277A (en) | 1979-01-11 |
| NO772510L (no) | 1978-01-17 |
| JPS5311983A (en) | 1978-02-02 |
| GB1589095A (en) | 1981-05-07 |
| HU178728B (en) | 1982-06-28 |
| CA1112799A (en) | 1981-11-17 |
| IT1064663B (it) | 1985-02-25 |
| YU145882A (en) | 1983-10-31 |
| CH628909A5 (en) | 1982-03-31 |
| NL7707832A (nl) | 1978-01-18 |
| NO147214B (no) | 1982-11-15 |
| YU145782A (en) | 1983-10-31 |
| BE856867A (fr) | 1978-01-16 |
| YU174977A (en) | 1982-10-31 |
| ZA774264B (en) | 1978-06-28 |
| NO147214C (no) | 1983-02-23 |
| FR2358429B1 (enrdf_load_stackoverflow) | 1981-05-22 |
| DE2732110A1 (de) | 1978-01-19 |
| DK323377A (da) | 1978-01-17 |
| DD130483A5 (de) | 1978-04-05 |
| IL52475A0 (en) | 1977-10-31 |
| AU512515B2 (en) | 1980-10-16 |
| GB1589096A (en) | 1981-05-07 |
| GB1589097A (en) | 1981-05-07 |
| IL52475A (en) | 1981-10-30 |
| SE7708247L (sv) | 1978-01-17 |
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